| Summary: | 碩士 === 國立交通大學 === 應用化學系碩博士班 === 99 === This thesis is divide into two parts:
1. Solvent participating one-pot glycosylation (SPOG) strategy was developed on the base of low concentration beta-selective glycosylation method. This strategy enables the control of stereochemistry in one-pot glycosylations through solvent addition. Meanwhile, further application of the low concentratnion glycosylation (LCG) to orthogonal glycosylation strategy is explored. Combining glycosyl phosphates and thioglycosides, oligosaccharides could be synthesized in a one-pot manner to furnish in good yield and excellent stereoselectivity.
2. Glucosamine is one of the major amino sugars present in human-related oligosaccharides, which contain an amino group (or acetamido) at the C-2 position. The azido function can readily be reduced to amine under mild conditions. Due to the non-participation nature, 2-azido-2-deoxy glycosyl donors are mandatory substrates for construction of 1,2-cis apha-glycosidic bond under specific reaction condition We developed a high-yielding and stereocontolled construction of 1,2-trans-beta-glycosidic linkages with 2-azido-2- deoxy glycopyranosyl donors using the solvent participated one-pot glycosylation strategy. We successfully prepared some biological relevant oligosaccharide targets such as F1-apha precursor trisaccharide, and beta-(1,6) glucosamine.
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